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First Step for Permits

I'll be filming a short film in late August and I've found a few locations that I need to try and lock down. The big one is an outdoor setting which takes place on a public road in a rural town. Along this road are maybe three or four houses and shutting down the road for a day would actually be very simple as it is not a high traffic area (it's a back road). My question is, do I approach the land owners first, seeing if they'd be willing to have me film along the road and on their property (about only 50 feet off the road) or do I approach the township first to get permission to film on the public road? Any ideas would be greatly appreciated.
 
Both.

It's a public road, so you'll need to talk to the city/town/village; especially since you want to shut the road down.

You'll also need to talk to the land owner, since you aim to be on their private property.
 
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